CN103172492B - Preparation method of sec-butyl alcohol - Google Patents
Preparation method of sec-butyl alcohol Download PDFInfo
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- CN103172492B CN103172492B CN201110438102.8A CN201110438102A CN103172492B CN 103172492 B CN103172492 B CN 103172492B CN 201110438102 A CN201110438102 A CN 201110438102A CN 103172492 B CN103172492 B CN 103172492B
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Abstract
The invention relates to a preparation method of sec-butyl alcohol. According to the preparation method, sec-butyl acetate generated through reaction between mixed C4 fractions and acetic acid is used as a raw material and is directly hydrogenated under the action of a copper-based solid catalyst to prepare sec-butyl alcohol with coproduct being ethanol, and in a fixed bed reactor the feed mass space velocity of sec-butyl acetate is 0.1-2.0h＜-1＞, the molar ratio of hydrogen to sec-butyl acetate is (2-40):1, the reaction temperature is 200-280 DEG C and the reaction pressure is 2.0-9.0MPa to directly prepare sec-butyl alcohol and cogenerate ethanol. The detailed preparation method refers to the specification. The conversion per pass of sec-butyl acetate is over 95%, the selectivity of sec-butyl alcohol is over 95% and ethanol is coproduced. The preparation method has the advantages that the energy consumption is reduced; circulation of mass raw materials is not needed, so the process flow is shortened; no other wastes are generated, so the process is clean; and separation is simple.
Description
Technical field
A kind of a kind of the present invention relates to preparation method of rudimentary Organic Alcohol, in particular it relates to system of sec-butyl alcohol
Preparation Method, the sec-Butyl Acetate being generated with acetic acid reaction with mixing C 4 fraction is raw material, and Hydrogenation is for sec-butyl alcohol（2- butanol）
The method of producing and ethanol in parallel.
Background technology
The raw material that sec-butyl alcohol is mainly used as solvent and produces butanone.The preparation method of sec-butyl alcohol has indirect hydration method and straight
Water receiving is legal.
Indirect hydration method is by n-butene Sulfation, then with this sulfuric ester of steam hydrolysis, thus obtaining Zhong Ding
Alcohol.In the method due to using sulphuric acid, do not only exist that corrosion of equipment, sulfur waste acid treatment, side reaction be many, technological process is complicated,
And energy consumption is big, now substantially free from commercial plant.
Direct hydration method is under acidic catalyst effect, and sec-butyl alcohol is prepared in n-butene and water reaction.Earliest is direct
Hydration method prepares sec-butyl alcohol, is that front Germany was succeeded in developing in 1984, and this technique is with strong-acid ion exchange resin for urging
Agent, 150-170 DEG C, 5-7MPa, water/n-butene mol ratio be 15：1-20：React under 1 process conditions, n-butene one way
Conversion ratio is 4-6%, and the sec-butyl alcohol of generation is substantially completely dissolved in C4 hydrocarbon, through oil-water separation, de- C 4 fraction and product purification etc.
Operation obtains.
Prepare sec-butyl alcohol process efficiency for improving direct method, many research workers propose process modification measure, such as English
Disclose in state's patent 1374368 and 1386195 and improve water/n-butene mol ratio to 100-173：1, raw material n-butene is once
Pass through, n-butene conversion per pass is up to 70%, but produces a large amount of enol water, and sec-butyl alcohol cannot reclaim, and raw material also cannot be fully
Using.And in United States Patent (USP) USP4476333 and USP4831197, disclose the technique using little water/n-butene mol ratio, will be big
Partly not anti-n-butene is mixed with fresh n-butene and is hydrated, and part n-butene is discharged outside battery limit (BL).This technique and flood/just
Butene molar ratio technique is compared has obvious superiority, is adopted by industry.But due to discharge unit not butylene anyway, raw material
Loss is big, and n-butene total conversion is not high.
It is respectively adopted highly acidic cation in addition, also disclosing that in Chinese patent CN101289368A and CN101395111A
Resin and heteropoly acid are the n-butene direct hydration technique of catalyst.The type technique is to produce the main flow side of sec-butyl alcohol at present
Method, is required to for mixing C 4 fraction to first pass through gas fractionation unit, obtains high concentration n-butene raw material, then make in acidic catalyst
Prepare sec-butyl alcohol, the conversion per pass general only 6% about of n-butene, a large amount of n-butene circulations, energy consumption with lower with water reaction
High.
Content of the invention
It is an object of the invention to overcoming the shortcomings of the prior art, and propose that yield is high, energy consumption is low
A kind of preparation method of sec-butyl alcohol.
The present invention seeks to being achieved by the following measures：The preparation method of sec-butyl alcohol：Anti- with acetic acid with mixing C 4 fraction
The sec-Butyl Acetate that should generate is raw material, in the presence of copper-base solid catalyst, in fixed bed reactors, sec-Butyl Acetate
Feedstock quality air speed is 0.1-2.0h-1, hydrogen is 2-40 with the mol ratio of sec-Butyl Acetate：1, reaction temperature is 200-280 DEG C,
Reaction pressure is 2.0-9.0MPa, and hydrogenation directly prepares sec-butyl alcohol, the method for producing and ethanol in parallel.
It is aluminium oxide catalyst, copper chromium that described copper-based catalysts include the supported copper oxide of infusion process preparation and carrier
Oxide catalyst, Copper-zinc oxide catalyst or its mixture.
The feedstock quality air speed of described sec-Butyl Acetate is preferably 0.1-1.0h-1.
Described hydrogen is preferably 10-20 with the mol ratio of raw material sec-Butyl Acetate：1.
Described reaction temperature is 220-260 DEG C.
Present invention firstly provides the sec-Butyl Acetate generating is reacted as raw material with mixing C4 with acetic acid, sec-Butyl Acetate raw material
Preparation method be：Mixing C 4 fraction and the acetic acid sec-Butyl Acetate that additive reaction generates under acidic catalyst effect, the party
Method industrialization.Then, by sec-Butyl Acetate raw material in the presence of copper-based catalysts, direct hydrogenation prepares sec-butyl alcohol co-production
The method of ethanol.
Compared with the method prepares sec-butyl alcohol technology with existing n-butylene hydration, there is following advantage：
1st, to mix the sec-Butyl Acetate that C 4 fraction and acetic acid additive reaction generate as raw material, separate without n-butene and fill
Put, reducing energy consumption；
2nd, under copper-base solid catalyst action, direct hydrogenation prepares sec-butyl alcohol, the list of sec-Butyl Acetate to sec-Butyl Acetate
Journey conversion ratio up to more than 95%, need not feedstock circulation in a large number, shortened process, reducing energy consumption, process cleans；
3rd, with sec-Butyl Acetate as raw material, during sec-butyl alcohol is prepared using fixed bed reactors direct hydrogenation, will be at a low price
Value carbinol derivatives acetic acid is converted into high value ethanol, and process economy is high；No other garbages produce, process cleans；
4th, sec-Butyl Acetate direct hydrogenation prepares sec-butyl alcohol technique, and product is sec-butyl alcohol and alcohol mixture, generates target
The selectivity of product sec-butyl alcohol, more than 98%, separates simple.
Specific embodiment
Supported copper oxide prepared by infusion process and carrier are aluminium oxide catalyst, Copper-Chromium Oxide Catalysts, copper zinc
One of oxide catalyst or its mixture, fill in fixed bed reactors, the Gao Jing of reactor（Gao Jing refers to react
The ratio of the direct and catalyst bed layer height of device, to meet reaction mass transfer requirement, is also typically will of catalytic multi-phase reactor
Ask）Than more than 6；Raw material sec-Butyl Acetate passes through dosing pump by regulation flow, mixes feeding fixed bed with the hydrogen through metering
In reactor, with the copper-based catalysts haptoreaction in filling and fixed bed reactors；Gas-liquid is entered after reacting rear material cooling
Separator, the non-antihydrogen gas that gas-liquid separator top is discharged is returned after hydrogen gas compressor compression and is mixed as anti-with fresh hydrogen
Should feed；The sec-butyl alcohol generating for reaction and the mixture of co-producing ethanol are discharged in gas-liquid separator bottom, are directly entered product and divide
From tower, obtain product sec-butyl alcohol and ethanol.
7 example examples are set forth below, the method for the present invention will be further described, but not only limit these enforcements
Example.
Embodiment 1
10 g active components are aoxidized the solid catalyst that copper content is 5%（Self-control, using equi-volume impregnating by 5% oxygen
Change copper to be carried on the column alumina support through 540 DEG C of roasting preparations）Fill in volume be 40 milliliters of internal diameters be 10mm not
In rust steel fixed bed reactors, the inertia quartz sand of using up and down of beds is filled；Reaction temperature is added by the outer electric furnace of reactor
Heat, temperature is placed in the armour formula thermocouple measurement in reactor catalyst bed, and reaction temperature controls at 200 DEG C；Reaction raw materials vinegar
By measuring after pump-metered, 5g pumps into reactor to the secondary butyl ester of acid on an hourly basis, and that is, reaction mass air speed is 0.5h-1；By hydrogen and vinegar
The raw materials components mole ratio of the secondary butyl ester of acid is 4：1, reaction raw materials hydrogen is mixed with raw material sec-Butyl Acetate after mass flowmenter
Enter reactor；Counterbalance valve is set after reactor, and regulation reaction pressure is 3.0MPa；Enter gas-liquid after product is condensed to divide
From device, non-antihydrogen gas empties after gas flowmeter metering, by gas-liquid separator bottom collection product.Reaction 8 hours, often
Hour is collected sample and is made up of gas chromatographic analysiss product, and calculates conversion ratio and the selection to sec-butyl alcohol of sec-Butyl Acetate
Property.Result of the test is：Sec-Butyl Acetate conversion ratio 95%, the selectivity to sec-butyl alcohol is 98%, and generating by-product isobutanol is 2%,
Remaining is ethanol.
Embodiment 2
10 g active components are aoxidized the solid catalyst that copper content is 10%（Preparation method is with embodiment 1）Fill in reality
Apply in reactor in example 1, reaction temperature controls at 220 DEG C；1g pumps into reactor, that is, to reaction raw materials sec-Butyl Acetate on an hourly basis
Reaction mass air speed is 0.1h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 8：1；Reaction pressure is 4.0MPa；Reaction
8 hours, collect sample per hour and be made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to sec-butyl alcohol
Selectivity.Result of the test is：Sec-Butyl Acetate conversion ratio 98%, the selectivity to sec-butyl alcohol is 97%, generates by-product isobutyl
The selectivity of alcohol is 3%, and remaining is ethanol.
Embodiment 3
10 g active components are aoxidized the solid catalyst that copper content is 15%（Preparation method is with embodiment 1）Fill in reality
Apply in reactor in example 1, reaction temperature controls at 240 DEG C；15g pumps into reactor to reaction raw materials sec-Butyl Acetate on an hourly basis,
I.e. reaction mass air speed is 1.5h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 8：1；Reaction pressure is 6.0MPa；Instead
Answer 8 hours, collect sample per hour and be made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to Zhong Ding
The selectivity of alcohol.Result of the test is：Sec-Butyl Acetate conversion ratio 96%, the selectivity to sec-butyl alcohol is 99%, generates by-product different
The selectivity of butanol is 1%, and remaining is ethanol.
Embodiment 4
10 g active components are aoxidized the solid catalyst that copper content is 25%（Preparation method is with embodiment 1）Fill in reality
Apply in reactor in example 1, reaction temperature controls at 260 DEG C；10g pumps into reactor to reaction raw materials sec-Butyl Acetate on an hourly basis,
I.e. reaction mass air speed is 1.0h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 10：1；Reaction pressure is 8.0MPa；
Reaction 8 hours, collects sample per hour and is made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to secondary
The selectivity of butanol.Result of the test is：Sec-Butyl Acetate conversion ratio 98%, the selectivity to sec-butyl alcohol is 99%, generates by-product
The selectivity of isobutanol is 1%, and remaining is ethanol.
Embodiment 5
It is 15% that 10 g active components are aoxidized copper content, containing the second auxiliary agent zinc oxide, the mol ratio of zinc oxide and copper oxide
For 1.5：1 solid catalyst（Preparation method is with embodiment 1, first oxide impregnation zinc oxide impregnation copper again）Fill in embodiment 1
In reactor, reaction temperature controls at 280 DEG C；10g pumps into reactor to reaction raw materials sec-Butyl Acetate on an hourly basis, i.e. reaction substance
Amount air speed is 1.0h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 15：1；Reaction pressure is 6.0MPa；React 8 little
When, collect sample per hour and be made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to sec-butyl alcohol
Selectivity.Result of the test is：Sec-Butyl Acetate conversion ratio 99%, the selectivity to sec-butyl alcohol is 99%, generates by-product isobutanol
Selectivity be 1%, remaining be ethanol.
Embodiment 6
By 10 g cupric and chromic oxide solid catalysts（Outsourcing, Taiyuan glad power catalyst plant）Fill in reaction in embodiment 1
In device, reaction temperature controls at 260 DEG C；20g pumps into reactor to reaction raw materials sec-Butyl Acetate on an hourly basis, and that is, reaction mass is empty
Speed is 2.0h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 20：1；Reaction pressure is 6.0MPa；Reaction 8 hours, often
Hour is collected sample and is made up of gas chromatographic analysiss product, and calculates conversion ratio and the selection to sec-butyl alcohol of sec-Butyl Acetate
Property.Result of the test is：Sec-Butyl Acetate conversion ratio 96%, the selectivity to sec-butyl alcohol is 97%, generates the choosing of by-product isobutanol
Selecting property is 3%, and remaining is ethanol.
Embodiment 7
By 10 g Copper-zinc oxide solid catalysts（Outsourcing, Taiyuan glad power catalyst plant）Fill in reaction in embodiment 1
In device, reaction temperature controls at 240 DEG C；10g pumps into reactor to reaction raw materials sec-Butyl Acetate on an hourly basis, and that is, reaction mass is empty
Speed is 1.0h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 40：1；Reaction pressure is 9.0MPa；Reaction 8 hours, often
Hour is collected sample and is made up of gas chromatographic analysiss product, and calculates conversion ratio and the selection to sec-butyl alcohol of sec-Butyl Acetate
Property.Result of the test is：Sec-Butyl Acetate conversion ratio 95%, the selectivity to sec-butyl alcohol is 98%, generates the choosing of by-product isobutanol
Selecting property is 2%, and remaining is ethanol.
Claims (5)
1. a kind of preparation method of sec-butyl alcohol it is characterised in that：The sec-Butyl Acetate being generated with acetic acid reaction with mixing C 4 fraction
For raw material, it is 10 mm that 10 g active components aoxidize the solid catalyst that copper content is 5% to be filled in volume for 40 milliliters of internal diameters
Rustless steel fixed bed reactors in, beds up and down use inertia quartz sand fill；Reaction temperature is by reactor dispatch from foreign news agency
Stove heat, temperature is controlled at 200 DEG C by the armour formula thermocouple measurement being placed in reactor catalyst bed, reaction temperature；Reaction
By measuring after pump-metered, 5 g pump into reactor to raw material sec-Butyl Acetate on an hourly basis, and that is, reaction mass air speed is 0.5 h-1；Press
Hydrogen is 4 with the raw materials components mole ratio of sec-Butyl Acetate:1, reaction raw materials hydrogen after mass flowmenter with raw material sec-Butyl Acetate
Be mixed entrance reactor；Counterbalance valve is set after reactor, and regulation reaction pressure is 3.0 MPa；After product is condensed
Enter gas-liquid separator, non-antihydrogen gas empties after gas flowmeter metering, by gas-liquid separator bottom collection product；Instead
Answer 8 hours, collect sample per hour and be made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to Zhong Ding
The selectivity of alcohol；Result of the test is：Sec-Butyl Acetate conversion ratio 95%, the selectivity to sec-butyl alcohol is 98%, generates by-product different
Butanol is 2%, and remaining is ethanol；Wherein, described active component oxidation copper content is that 5% solid catalyst is, using equal-volume
5% copper oxide is carried on the column alumina support through 540 DEG C of roasting preparations infusion process.
2. a kind of preparation method of sec-butyl alcohol it is characterised in that：The sec-Butyl Acetate being generated with acetic acid reaction with mixing C 4 fraction
For raw material, it is 10 that 10 g active components aoxidize the solid catalyst that copper content is 10% to be filled in volume for 40 milliliters of internal diameters
In the rustless steel fixed bed reactors of mm, the inertia quartz sand of using up and down of beds is filled；By the outer heating by electric cooker of reactor,
Temperature is controlled at 220 DEG C by the armour formula thermocouple measurement being placed in reactor catalyst bed, reaction temperature；Reaction raw materials vinegar
By measuring after pump-metered, 1 g pumps into reactor to the secondary butyl ester of acid on an hourly basis, and that is, reaction mass air speed is 0.1 h-1；By hydrogen with
The raw materials components mole ratio of sec-Butyl Acetate is 8:1；Reaction raw materials hydrogen mixes one with raw material sec-Butyl Acetate after mass flowmenter
Rise and enter reactor；Counterbalance valve is set after reactor, and regulation reaction pressure is 4.0 MPa；Gas is entered after product is condensed
Liquid/gas separator, non-antihydrogen gas empties after gas flowmeter metering, by gas-liquid separator bottom collection product；React 8 little
When, collect sample per hour and be made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to sec-butyl alcohol
Selectivity；Result of the test is：Sec-Butyl Acetate conversion ratio 98%, the selectivity to sec-butyl alcohol is 97%, generates by-product isobutanol
For 3%, remaining is ethanol；Wherein, described active component oxidation copper content is that 10% solid catalyst is, using incipient impregnation
10% copper oxide is carried on the column alumina support through 540 DEG C of roasting preparations method.
3. a kind of preparation method of sec-butyl alcohol it is characterised in that：The sec-Butyl Acetate being generated with acetic acid reaction with mixing C 4 fraction
For raw material, it is 10 that 10 g active components aoxidize the solid catalyst that copper content is 15% to be filled in volume for 40 milliliters of internal diameters
In the rustless steel fixed bed reactors of mm, the inertia quartz sand of using up and down of beds is filled；By the outer heating by electric cooker of reactor,
Temperature is controlled at 240 DEG C by the armour formula thermocouple measurement being placed in reactor catalyst bed, reaction temperature；Reaction raw materials vinegar
By measuring after pump-metered, 15 g pump into reactor to the secondary butyl ester of acid on an hourly basis, and that is, reaction mass air speed is 1.5 h-1；By hydrogen with
The raw materials components mole ratio of sec-Butyl Acetate is 8:1；Reaction raw materials hydrogen mixes one with raw material sec-Butyl Acetate after mass flowmenter
Rise and enter reactor；Counterbalance valve is set after reactor, and regulation reaction pressure is 6.0 MPa；Gas is entered after product is condensed
Liquid/gas separator, non-antihydrogen gas empties after gas flowmeter metering, by gas-liquid separator bottom collection product；React 8 little
When, collect sample per hour and be made up of gas chromatographic analysiss product, and calculate the conversion ratio of sec-Butyl Acetate and to sec-butyl alcohol
Selectivity；Result of the test is：Sec-Butyl Acetate conversion ratio 96%, the selectivity to sec-butyl alcohol is 99%, generates by-product isobutanol
For 1%, remaining is ethanol；Wherein, described active component oxidation copper content is that 15% solid catalyst is, using incipient impregnation
15% copper oxide is carried on the column alumina support through 540 DEG C of roasting preparations method.
4. a kind of preparation method of sec-butyl alcohol it is characterised in that：The sec-Butyl Acetate being generated with acetic acid reaction with mixing C 4 fraction
For raw material, it is 10 that 10 g active components aoxidize the solid catalyst that copper content is 25% to be filled in volume for 40 milliliters of internal diameters
In the rustless steel fixed bed reactors of mm, the inertia quartz sand of using up and down of beds is filled；By the outer heating by electric cooker of reactor,
Temperature is controlled at 260 DEG C by the armour formula thermocouple measurement being placed in reactor catalyst bed, reaction temperature；Reaction raw materials acetic acid
By measuring after pump-metered, 10 g pump into reactor to secondary butyl ester on an hourly basis, and that is, reaction mass air speed is 1.0 h-1；By hydrogen and vinegar
The raw materials components mole ratio of the secondary butyl ester of acid is 10:1；Reaction raw materials hydrogen is mixed with raw material sec-Butyl Acetate after mass flowmenter
Enter reactor；Counterbalance valve is set after reactor, and regulation reaction pressure is 8.0 MPa；Gas-liquid is entered after product is condensed
Separator, non-antihydrogen gas empties after gas flowmeter metering, by gas-liquid separator bottom collection product；Reaction 8 hours,
Collect sample per hour to be made up of gas chromatographic analysiss product, and calculate conversion ratio and the selection to sec-butyl alcohol of sec-Butyl Acetate
Property；Result of the test is：Sec-Butyl Acetate conversion ratio 98%, the selectivity to sec-butyl alcohol is 99%, and generating by-product isobutanol is 1%,
Remaining is ethanol；Wherein, described active component oxidation copper content is that 25% solid catalyst is, will using equi-volume impregnating
25% copper oxide is carried on the column alumina support through 540 DEG C of roasting preparations.
5. a kind of preparation method of sec-butyl alcohol it is characterised in that：The sec-Butyl Acetate being generated with acetic acid reaction with mixing C 4 fraction
For raw material, it is 15% that 10 g active components are aoxidized copper content, zinc oxide containing auxiliary agent, and zinc oxide with the mol ratio of copper oxide is
1.5:1 solid catalyst fill in volume be 40 milliliters of internal diameters be catalyst in the rustless steel fixed bed reactors of 10 mm
The inertia quartz sand of using up and down of bed is filled；By the outer heating by electric cooker of reactor, temperature is by being placed in reactor catalyst bed
Armour formula thermocouple measurement, reaction temperature controls at 280 DEG C；Reaction raw materials sec-Butyl Acetate by measuring after pump-metered, on an hourly basis
10 g pump into reactor, and that is, reaction mass air speed is 1.0 h-1；Raw materials components mole ratio by hydrogen and sec-Butyl Acetate is 15:1；Instead
Raw hydrogen is answered to be mixed with raw material sec-Butyl Acetate after mass flowmenter entrance reactor；Back pressure is set after reactor
Valve, regulation reaction pressure is 6.0 MPa；Gas-liquid separator is entered, non-antihydrogen gas is through gas flowmeter after product is condensed
Empty after metering, by gas-liquid separator bottom collection product；Reaction 8 hours, collects sample per hour and is divided by gas chromatogram
Division thing forms, and calculates conversion ratio and the selectivity to sec-butyl alcohol of sec-Butyl Acetate；Result of the test is：Sec-Butyl Acetate turns
Rate 99%, the selectivity to sec-butyl alcohol is 99%, and generating by-product isobutanol is 1%, and remaining is ethanol；Wherein, described activearm
Oxidation copper content is divided to be 15%, zinc oxide containing auxiliary agent, zinc oxide is 1.5 with the mol ratio of copper oxide:1 solid catalyst is to adopt
Quantitative copper oxide and zinc oxide are carried on the column alumina support through 540 DEG C of roasting preparations by two step equi-volume impregnatings
On, described two step equi-volume impregnatings are first oxide impregnation zinc oxide impregnation copper again.
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104475109A (en) * | 2014-11-20 | 2015-04-01 | 北京恩泽福莱科技有限公司 | Catalyst for preparing sec-butyl alcohol and preparation method of catalyst |
| CN105618062A (en) * | 2014-11-26 | 2016-06-01 | 江苏海普功能材料有限公司 | Sec-butyl acetate hydrogenation catalyst, preparation method and application thereof |
| CN104402671B (en) * | 2014-12-11 | 2015-09-09 | 湖南瑞源石化股份有限公司 | A kind of acetic acid C3-C5 alkyl ester hydrogenation produces the technique of C3-C5 alkyl alcohol co-production ethanol |
| CN104478676B (en) * | 2014-12-11 | 2016-03-16 | 湖南瑞源石化股份有限公司 | Preparation and the refining system of butanone |
| CN105126798B (en) * | 2015-07-29 | 2018-04-13 | 上海华谊（集团）公司 | Sec-butyl acetate is hydrogenated with catalyst of coproduction sec-butyl alcohol and ethanol and its preparation method and application |
| CN105032439A (en) * | 2015-07-29 | 2015-11-11 | 上海华谊（集团）公司 | Catalyst for producing sec-butyl alcohol and ethyl alcohol through sec-butyl acetate hydrogenationm, preparation method and application thereof |
| CN106554251A (en) * | 2015-09-25 | 2017-04-05 | 中国石油化工股份有限公司 | A kind of method that C-4-fraction prepares sec-butyl alcohol and ethanol after utilization ether |
| CN105503526A (en) * | 2016-01-18 | 2016-04-20 | 上海华谊（集团）公司 | Method for producing sec-butyl alcohol and co-producing ethanol through sec-butyl acetate hydrogenation |
| CN105732312B (en) * | 2016-03-25 | 2018-02-23 | 北京石油化工学院 | A kind of overcritical Hydrogenation of sec-Butyl Acetate for sec-butyl alcohol co-producing ethanol method |
| CN107540522B (en) * | 2016-06-29 | 2020-09-08 | 中国石油化工股份有限公司 | Production process of sec-butyl alcohol |
| CN110639623B (en) * | 2019-11-12 | 2023-10-20 | 淄博齐翔腾达化工股份有限公司 | Activation method and reaction device for preparing methyl ethyl ketone catalyst by dehydrogenating sec-butyl alcohol |
| CN115894171B (en) * | 2022-11-17 | 2024-04-16 | 凯瑞环保科技股份有限公司 | Method for preparing sec-butyl alcohol by hydrogenating sec-butyl acetate |
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